title: Design and synthesis of hydroxypyridinone-L-phenylalanine conjugates as potential tyrosinase inhibitors.
abstract: A range of hydroxypyridinone-L-phenylalanine conjugates were synthesized starting from kojic acid. Their tyrosinase activity was determined, and it was found that one of the compounds ((S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate, 5e) showed potent inhibitory effect against mushroom tyrosinase, the IC50 values for monophenolase and diphenolase activities being 12.6 and 4.0 μM, respectively. It was also demonstrated that these conjugates are mixed-type inhibitors, suggesting they could bind to both the free enzyme and the enzyme-substrate complexes. MTT assay indicated that 5e was nontoxic to three cell lines. This compound may find applications in food preservation and cosmetics.
authors.affiliation: School of Food Science and Biotechnology, Zhejiang Gongshang University , Hangzhou, Zhejiang 310035, People's Republic of China.
authors.forename: Dong-Fang
authors.initials: DF
authors.lastname: Li
authors.forename: Pan-Pan
authors.initials: PP
authors.lastname: Hu
authors.forename: Mu-Song
authors.initials: MS
authors.lastname: Liu
authors.forename: Xiao-Le
authors.initials: XL
authors.lastname: Kong
authors.forename: Jin-Chao
authors.initials: JC
authors.lastname: Zhang
authors.forename: Robert C
authors.initials: RC
authors.lastname: Hider
authors.forename: Tao
authors.initials: T
authors.lastname: Zhou
mesh_terms: D000363:Agaricales / Q000737:chemistry / Q000201:enzymology*; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D005656:Fungal Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D010649:Phenylalanine / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry
chemical_list: D004791:Enzyme Inhibitors; D005656:Fungal Proteins; D011728:Pyridones; D011753:Pyrones; D010649:Phenylalanine; C011890:kojic acid; D014442:Monophenol Monooxygenase